Non-destructive Removal of the Bornanesultam Auxiliary in α-Substituted <i>N</i>-Acylbornane-10,2-sultanis under Mild Conditions: An efficient Synthesis of Enantiomerically Pure Ketones and Aldehydes

Article Article scientifique Article Non-destructive Removal of the Bornanesultam Auxiliary in α-Substituted <i>N</i>-Acylbornane-10,2-sultanis under Mild Conditions: An efficient Synthesis of Enantiomerically Pure Ketones and Aldehydes eng 1997 author Von Oppolzer Wolfgang 25270 author Darcel Christophe 106242 author Rochet Patrick 99932 author Rosset Stéphane 28170 author De Brabander Jef 30115 1319-1337 10.1002/hlca.19970800502 0018-019X http://doi.wiley.com/10.1002/hlca.19970800502 α‐Substituted N‐acylbornane‐10, 2‐sultams 6, 9, and 10 can be converted into enantiomerically pure ketones 5. 13, and 14, respectively, via a two‐step procedure involving a known mercaptolysis reaction followed by an [Fe(acac)₃]‐mediated coupling of the resulting S‐benzyl thioesters with Grignard reagents. Furthermore, enantiomerically pure aldehydes 23 can be obtained from α‐substituted N‐acylbornane‐10,2‐sultams 6 via a one‐step reduction with (i‐Bu)₂AIH. No epimerization at the α‐chiral center is observed during the cleavage reaction whereby the chiral auxiliary, bornane‐10,2‐sultam 1 or ent‐l, was recovered. By using this methodology, several natural products or precursors thereof can be prepared. Dewey 540 36 Département de chimie organique 141 false Helvetica Chimica Acta 80 5 bcea220b-5279-4476-8899-0f39c13ccd3f Article (Published version) Restricted Oppolzer_et_al-1997-Helvetica_Chimica_Acta-1.pdf 1392311 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Non-destructive Removal of the Bornanesultam Auxiliary in α-Substituted N-Acylbornane-10,2-sultanis under Mild Conditions: An efficient Synthesis of Enantiomerically Pure Ketones and Aldehydes	Helvetica Chimica Acta			1997	307	0

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Rochet, Patrick